A good friend of mine from junior high was in a movie with Gary Sinise, who was in Apollo 13 with Kevin Bacon, so that puts me way close to just about everyone, considering I don’t work in the entertainment industry.
In my writing days, I interviewed quite a few nationally known musicians, but I think only afew would remember me.
My friend T’s brother J dated Mary Chapin Carpenter.
My friend C’s friend S dated a guy who dumped her for Bjork.
Our next-door neighbor made rugs for Happy Rockefeller.
I once played a gig with Gary “U.S.” Bonds, who was in the (terrible) Blues Brothers 2000. That gets me linked up to folks like Dan Aykroyd and Eric Clapton.
Being able to play bass with Gary on the song “New Orleans” was one of the great moments in my musical life.
I met Howie Mandel back in the blown-up surgical glove/chicken days.
A friend of a friend was Randy Rhoads, lead guitarist of Quiet Riot and then for Ozzie Osbourne, the latter only for a couple of years before he died in a plane crash. We saw him at the Whisky several times via the guest list, when the Whisky was still a good club.
My father had numerous celebs come in for insurance screening, when he was in medical practice. I remember him talking about the Beach Boys, who for some reason definitely didn’t want their blood drawn that day (this was the height of the 1960s).
My brother used run a pool route, so he knows a fair number also.
Something I never knew until a few years ago is that my late uncle was an actor and did lots of extra type work. His last gig: Stir of Echoes with Le Bacon.
Chuck Norris’s niece was a childhood friend of mine (and no, she could not divide by zero).
My family’s closest friend’s lived in West Hollywood and had a number of fairly close relationships with celebrities, but for some reason the one that comes to mind is Zara “Mother Jefferson” Cully of the Jeffersons. She lived in their buidling and was present at many of our gatherings (of course I was about six, so really didn’t care, but still . . .)
But my most exciting association (to me) is that I worked with Johnny “Vatos” Hernandez"s wife (he was the drummer for Oingo Boingo) and I not only got to go to many O B gigs and parties, but I also got some secondhand furniture and a TV from them.
That reminds me, my dad grew up on the SoCal coast and used to hang out with the Beach Boys, before they got big. They’d be at beach parties and such.
Added note; At least that’s what he told me. I really can’t verify if his stories are true.
Oh, another couple. My best friend in high school’s brother lived next door to Jimmy Buffet in Key West. I’ve also met Jimmy twice, so that gets me a big hunk of the rock and country music industry. My mom has volunteered for and worked closely with Rep. Jerry Lewis of California, which gets me the American political establishment, and via that, the world!
My aunt MaryJo was an extra in The Deer Hunter. I was an “extra” in the Goldie Hawn film Wildcats (and so was almost everyone I went to HS with, as it was filmed in part in my old neighborhood.)
Dennis Farina’s sister Bernadette is my great-aunt’s best friend, and he and his brother Roland are family friends through her as well.
My aunt Margaret went to high school with Harrison Ford.
As mentioned recently elsewhere, Anton LeVay was “married” to my cousin Diane.
My great-uncle Porky (yes, really - his real name was Frank, but everyone called him Porky) was the president of the Chicago Musicians’ Union for over 50 years, and my great-grandfather was a well-known jazz musician in the 20s and 30s. I can pretty easily connect to anyone in the music industry through them in less than 6 degrees.
I went to college with Marlee Matlin. (We had one class together.)
And I had dinner with John Wayne Gacy. (Which is a great way to derail a thread or conversation, I’ve found.)
I used to work for Bob Taft, governor of Ohio. Saw him every day in the elevator and at the coffee machine. He, I’m sure, knew Mike DeWine and Voinovich (the senators from OH), who I’m sure know Bush, Cheney, et al.
An ex-roommates mother went to prom with Ted Kaczynski.
My sister once shook hands with Bill Clinton at a rally.
I’ve bought Microsoft products, and you know if you go far back enough along the chain, you’ll get to Bill himself. And if that ain’t a close connection, I don’t know what is. 
I meant to say the nephew of a good friend of mine…
My aunt was married to a man who was a big supplier of persian rugs to the White House. She once met Richard Nixon at a reception of some sort. Does Nixon qualify as a celebrity? No? Well, as I’m sure we all know, Nixon once met Elvis!
I used to have a good friend, whom I’ve since lost contact with, whose mother gave Robert Plant guitar lessons when he was a kid.
One out of two ain’t bad. The missus says that in return I can have a go on Angelina - if she’ll have me. I have managed to negotiate that to Jen as well. 
I know an Earl, and he’s met the Queen plenty of times, so I reckon that puts me less than six degrees away from pretty much every world leader of the twentieth century.
I went to college with Kevin Eubanks and Branford Marsalis. I didn’t know them, but I knew people who knew them.
I was in a high school play with Cory English, who understudied for Nathan Lane in the Producers, costarring Matthew Broderick who was in Max Dugan Returns with Keifer Sutherland.
My father-in-law was pediatrician to Andre Braugher’s kids while they were living in Baltimore for the filming of “Homicide: Life on the Street”.
Forgot about my aunt, who “dated” Jim Morrison. She told me a story once about shooting up with him in some apartment once.
Gotta love the sixties.
This one’s pretty easy. My Godmother is a location manager in the film industry and has done the work on several Clint Eastwood films and other big-budget Hollywood films. That puts me one step from a lot of folks in Hollywood, although I’ve never met any celebrity because of her.
On my own, I’ve met M.C. Hammer and Mario Van Peebles, and I went to high school with Toby Bailey, who was a college superstar at UCLA and had a very brief NBA career.
Stepping out another degree, I am friends with the guy whose sister is married to French Stewart. :dubious:
I’m almost afraid to ask – What did you have?
My girlfriend ran into Bill Clinton once. Literally. The Secret Service was not thrilled.
Something served with a nice chianti.
My first concert evah! I wish I was you.